Dress for comfort and manoeuvrability. Always wear a PFD/lifejacket. Always bring a change of warm dry clothing. May to mid-June wear layers of neoprene, fleece, wool, gortex, and rubber as needed. July to August wear a windbreaker, shorts, and a t-shirt. Other useful items include a hat, sunglasses, sunscreen, and a bottle of water.
Rule of thumb
If the water is cold, always wear a wetsuit, even if the air is warm.
If it is windy or can get windy, always wear your foul weather gear (top and pants) and bring a winter hat with you.
Item by item
Wetsuit - full or shorty
You can get them at Mountain Equipment Coop $110, costco (shorty, ~$40) or Fogh marine. If the water is still cold a wet suit or dry suit (more $) will be needed. The best place in Toronto to get a full wetsuit is, we believe, Board Sport. O'Neill full wetsuit are currently (April 2014) on sale for $150+tax. If you take your lesson in May, make sure to wear a full wetsuit.
April to Mid-June wear layers of neoprene, fleece, wool, gortex and rubber as needed, skiing mid layer stuff is good. You will wear these over your wetsuit for insulation, no cotton, it will keep you cold. Don't worry as soon as summer hits you'll be in t-shirts! That sun better be shining this summer!
Foul weather gears (also known as splash gears)
Rain gear, you can get a set from Costco (~ $60) or Fogh Marine. Wind proof jacket and splash pants will work, not the cheap $5 kind, they will rip. This will keep you warm when the wind picks up
We highly recommend the gardening gloves you can get the regular nylon with rubber covering for gardening (picture here ~$5) If your hands get cold, then opt for some neoprene gloves (at MEC for $15)
You need them for grip when pulling in the sails and will want something that will keep you warm based on your own tolerance for cold hands. Your hands will get wet!
The best place to get them is at Fogh Marine and Genco Marine, price varies depending on brand. You need footwear for grip as you move around the boat and protection as there are many mounts and ropes that you'll be stepping over. Water will get into your boat and a pair of sailing boots will help keep your feet warm. Some people use old running shoes with neoprene socks to start with.
Change of clothing
Always bring a change of warm dry clothing and a towel. You'll want those cozy tops as the weather is colder down by the water. Don't throw out those old shorts! Clothing can get ripped on boat fittings.
Hat and Sunglasses
Other useful items include a hat (winter), sunglasses, sunscreen, a bottle of water.
Life jackets PFDs are always worn while sailing. Although the Club has some general use PDFs, during lessons there may not be enough to go around. It is recommended that you purchase your own PDF. Check the inside label to be sure it approved by Canada Coast Guard and it is sized correctly for your body weight. A PDF can be purchased for as cheap as $20-30 from Canadian Tire. Also, see Where to buy, following, for high performance models.
Yes it sounds extreme! But when your out there having fun you'll forget about the layers you have on, you'll be warm, happy and sailing! In the summer you'll be out there with the sunscreen on and a sun cap on enjoying the hot weather!